


Late Nights

by fuckingcommissions



Series: Max and Co Commissions [1]
Category: Pocket Monsters | Pokemon - All Media Types
Genre: Blow Job, Cunnilingus, F/M, Incest, Loss of Virginity, Masturbation, Omorashi, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2017-05-23
Updated: 2017-05-23
Packaged: 2018-11-04 02:47:23
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,104
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10981752
Author URL: https://archiveofourown.org/users/fuckingcommissions/pseuds/fuckingcommissions
Summary: Max happens upon May in the middle of the night.





	Late Nights

**Author's Note:**

> A different continuity of Pokemon commissions

It was late when Max woke up, realizing that he really needed to pee. He didn't like getting up in the dark, but he had gotten used to it during their time spent traveling, and it certainly beat the alternative, considering how he wanted everyone to stop treating him like a child. He got out of his tent and began looking through the woods for somewhere fairly private, when he heard a very strange noise.

It didn't sound like any Pokemon he had ever heard before and he wondered what it was, forgetting his need for a moment to go investigate. He was very curious as the noises got louder, and soon he could both pinpoint where they were coming from and tell that they had a feminine tone to them, more human than he had originally thought. Going deeper into the woods, he could tell that he was almost upon whatever the noises were.

Finally, he emerged from behind a tree and saw the source of the noises, something that absolutely shocked him. His big sister May was sitting against another tree with her flannel nightgown pulled up around her waist, her legs spread and her hand between them. She wasn't wearing anything under her gown, but she looked different than he did down there and he wasn't sure why. Was there something wrong with her or were all girls like that or just certain people?

Whatever the case, it looked more like a hole between her legs than anything else and she dug her fingers into it, making more of the strange noises that he had heard before. It had been her all along, doing whatever it was that she was doing. And he had no idea what she was doing, why she was touching herself like that or making those loud noises or anything, but she had her eyes closed and hadn't seemed to notice him approach her yet.

He got the feeling that this was something private for her, but he couldn't bring himself to leave and instead stood watching her. She had a look on her face that he had never seen before, she looked happy but it was almost more than that and her cheeks were flushed as she arched her back against the tree, pressing her finger deeper and moaning louder.

“Oh, yes,” she cried, and he was startled to hear her speaking. “Yeah, just like that! Oh, yeah, come on!” She let out another noise, this one sounding a bit more pained. “Please, I really have to pee!” He flinched at that statement, wondering what that had to do with this, if this was something you were supposed to do when that was the case.

“Oh, it hurts so much, I have to pee so bad,” she groaned. “Please, please, fuck me harder, I love it!” Again, she confused him. Did it hurt or did she love it? And what did 'fuck' mean? Who was she talking to? She hadn't acknowledged that he was there yet, so she couldn't be talking to him, but no one else was there.

“Please hurry, please, I have to pee, you know I won't last much longer, you know I can't hold it! I've been holding it for so long, please...oh, fuck me harder.” Every time she said that, she would pick up speed with her fingers, and Max wondered if that was what fucking was and if she was talking to herself. He knew that girls, especially his sister, were weird, but he had never known that they snuck off at night to do strange things like this!

But he as he watched her, he began to feel funny himself, a weird feeling in the pit of his stomach that extended all the way to his private bits that were so different than what May had. It felt so weird that he couldn't describe it and he didn't know why, but he found himself pulling it out of his shorts and taking it into his hand. That made it feel a bit better, but not nearly enough and so he began to stroke at it, rubbing his hand up and down while he watched May beg an imaginary someone to 'fuck' her.

“Hurry up and come,” she begged, once again confusing Max. Come where? From where? Who was she waiting for? “Please, before I make a big mess. Fuck me harder, please, I have to pee!” She was getting so repetitive and he wondered, if she needed to pee so bad, why she didn't already. When he thought that, he felt like he might be forgetting something, but he was too distracted watching her and touching himself that he didn't think much of it.

He didn't know what was happening and couldn't begin to comprehend it, but he was slowly realizing that he really liked it. One thing he did know was that he wasn't supposed to be watching, but he really couldn't help himself. He was absolutely fascinated and though touching himself helped, the weird feeling still wasn't going away and he didn't want to stop until he could make it go away for good. May seemed to be working toward the same goal, but what that goal was, he still didn't know.

“I'm not gonna make it, I'm not gonna make it!” she cried, and then she began to moan incoherently. She bucked her hips a few times and then let out one final, loud moan that faded into a low groan of relief as she began to pee. A foamy puddle hissed out of her, the ground not able to absorb it, there was so much of it. The puddle spread out and she removed her hand, seeming satisfied with what had happened.

He didn't know why she had had to pee for that to happen, or why he liked that she had so much. There was so much happening tonight that he couldn't understand, but he was trying so hard to finish himself off like his sister had that he just couldn't bring himself to worry about it. Maybe he would understand once he was done and he began to work at himself more frantically, desperate to reach the same release that his sister had.

Meanwhile, she still had her eyes closed, leaning back against the tree, looking too weak to support herself should she try to stand or even sit on her own. She looked like she felt really good and really happy, and he didn't think about the fact that he was standing out in the open and wasn't hidden in the slightest. At least, he didn't think about that until she opened her eyes, gasping and freezing when she saw him standing there.

And he froze as well, too terrified and guilty to move, his hand still where it had been, all too telling of what he had been doing. They stared at each other for a long while, neither one knowing what to say. Finally, after what felt like years, May finally said, “How long have you been standing there, Max?”

“I...I don't...”

“How much of that did you see?”

“I don't know! I just walked up and you were playing with your...with your...” He searched for the words he did not yet know. “You know, whatever you have instead of a thingy! And...and...then...” He trailed off, too afraid to go on. “I'm sorry!” he finally finished, not even sure how to explain what he had been doing.

He expected May to start going off on him, to rail on him for spying on her, but instead, she surprised him by smiling. She began to crawl towards him and he was not sure how he was supposed to react to that, so he simply stood there, watching her as she approached him. “Your little cock and balls are so cute,” she cooed, her breathing growing as labored as it had been when he found her like that.

“H-huh?” he asked. “My...what?”

“That's what grownups call...these,” she purred, gesturing with a hand before caressing him where he had been touching himself, causing him to shudder. Then she took what she referred to as his balls in her hands, fondling them while she brought his cock into her mouth, surprising him with how good that felt. He hissed as she sucked him and played with him, and it was so much better than touching himself alone.

It felt so good, in fact, that when she stopped and pulled back, he whined aloud from disappointment. “Why did you stop?” he asked, practically wailing. Though it felt good when she was doing it, now that she had stopped, he was back to being so desperate for contact that it hurt even worse than before.

“That was called a blow job,” she said, “and the reason I stopped is because that was just a warm up. Sometimes people can do just that, but that doesn't do much for me, so I think we should move on to other, better things. Do you want to do something better now?” Max nodded enthusiastically and she pulled off her nightgown, spreading it out on the ground and laying on top of it.

He watched her, transfixed as she spread her legs for him, giving him another good view of her. “Most grown ups call this a pussy,” she explained. “And here,” she reached a finger inside of her, showing him something, “is my clit. That is what makes me feel really good. And instead of getting blow jobs, girls get something called 'eating out', where boys like inside them. Especially the clit.”

He didn't wait for further instructions and instead dove between her legs, lapping at her enthusiastically. He pressed his tongue deep inside her folds, finding that she tasted very pleasant. It wasn't a taste he could really describe, but it was one that he knew that he liked quite a bit. He made sure to pay attention to the thing she had showed him, the thing she had called her clit, and she made a lot of happy noises when he did so, encouraging him to continue with his movements. He was very glad that his sister was proud of what he was doing; he felt like he had passed some sort of initiation to being more grown up.

“Oh, yeah, that's really good, Max,” she moaned. “You're doing such a good job!” Her approval meant the world to him and drove him further until she placed a hand on the back of his head and said, “Okay, that's enough of that. You're gonna finish me before we even make it to the main event!” He pulled his head back, looking at her, waiting for further instruction.

“Now, we're going to have sex,” she said, and he gasped aloud, because he had heard the word used before but had never known what it meant. Any attempts to find out had ended in him being told to wait until he was older, but now May was going to explain it to him. “What you do is you put your cute little cock into my pussy, and push in and out until we both feel really good.” He got on top of her after that, trying to figure out exactly how to do that, and she took his cock in hand, helping to guide him.

Just that small touch was enough to cause him to whine for more, but she soon let go of him once he was pressing right up against her entrance. “Just push into me,” she encouraged. “That's all you have to do.” Nodding, he slowly pressed into her, trying to do it like he had done with his tongue. There was not much difficulty and he slid into her with ease, small involve to fit without any trouble.

Being engulfed in her flesh like that was even better than being inside of her mouth, and being touched by his hand or her hand did not even come close to comparing. He let out a loud noise that she mimicked, and she rested her hands on the back of his head and bucked her hips up, causing more friction that made him cry out even louder. He was so overwhelmed with pleasure that he couldn't believe that this was something he had never known about before. How could anyone keep something that felt so good a secret for so long?  
“So good, May, it's so good,” he said, breathlessly. “Thank you so much...”

She took one hand and laid it on her chest. “My breasts,” she said. “Play with him, suck on them. That will feel really good for me too.” He nodded, trying to regain his composure enough to do such a thing. He reached one hand out, taking one of her breasts in his hand, marveling at how soft it was. He gave it a light squeeze then let it fall from his hand until he was touching her nipple, pinching at it experimentally. May let out a moan of such great pleasure that he knew he had done something right and began to roll it in his fingers.

“Oh, god, yes, Max!” she screamed. “Just like that, just like that! Now...now use your mouth on the other one.” He lowered his head, licking her other nipple tentatively, and she once against let out a cry of pleasure. He parted his lips, taking her breast into his mouth and sucking on it, rolling his tongue over it and trying to emulate what he did with his fingers on the other breast. Her pussy grew tighter and tighter around him and he felt so good that he could hardly stand it.

He continued doing what he could to her breasts, continued making sure that she was feeling just as good as he was. It was the least he could do to repay her for teaching so many things and showing him what it meant to be grown up. He considered himself very lucky that he had an older sister willing to help him like this even though there were times that they did not get along as well as they could. She really was the best sister in the whole world.

But then he felt a harsh pang in his bladder, very sharp and very painful. He had forgotten that the entire reason he had come out into the woods was because he had needed to pee so badly, and now he realized that he had gone so long without thinking about it that he was already at his very limit. He didn't want to stop doing this, but he knew that if he waited too long, it would end badly and that he needed to take a break, right away.

“May,” he moaned, pulling his mouth away from her. “May, I need to pee...I'm really sorry, but I have to pee so bad, we need to stop.”

Shaking her head, May said, “It's okay, Max.” Little did he know, she was confused and thought that he thought he was nearing an orgasm and had the two mixed up. She did not believe that he actually had to pee.

“But, May, if we don't stop...I'm not gonna make it,” he whined, knowing that he was already reaching his very limit. “I really can't hold it much longer!”

“Just let it out,” she urged. “I promise, you'll feel a lot better if you do and we don't have to stop.”  
He recalled when he had watched her earlier, how she had had to pee the entire time and had ended up peeing on the ground, and realized that that must be another part of sex that he hadn't known about. If she said that it was okay, then he supposed that it must be okay, and he really wasn't going to make it a moment longer. Before he could ask her another question, she caught his lips in a kiss, and he relaxed, letting his bladder empty into his sister.

His warm urine began filling her up, and she at first moaned into the kiss but then she realized that this was not an orgasm, that her little brother was actually peeing inside of her. She broke the kiss and groaned in disgust, saying, “Max, no, you're not supposed to actually pee in me!”

“But...but you said...” He couldn't even argue with her, he was so overcome with relief, and she was so tight around him that none of the liquid escaped her. It was all too good for him to handle.

“This is so...” She trailed off, moaning, because even though she thought she should hate this, she realized that it felt good, better than anything she had ever been able to do to herself, better even than having her little brother fuck her. She felt herself tightening up, a pulsing sensation rocking through her, and then she was over the edge, crying out as she reached her first orgasm with another person.

And Max could feel her spasming around him and that, coupled with the fantastic feeling of finally emptying his bladder, was too much for him. Finally, he felt as though he had reached the peak that he had been reaching for this whole time, and he felt absolutely amazing, whimpering his sister's name as he reached the first orgasm of his entire life.

When they both finally came down from it, panting in each other's arms, he said, “I'm sorry that I...”

“No, it's okay,” she replied. “I was just confused. I liked that.” She looked at them and giggled. “We're a mess, aren't we? Here, let's get cleaned up.” She helped him up and got a package of wipes that she had kept with her by the tree, and the two of them got themselves clean before she got dressed and they headed back for the campsite.

“Do you want to share my sleeping bag tonight?” she asked.

“Yeah!” he said happily, eager to cuddle with his big sister for the rest of the night.

~X~

“I've never seen the two of you get along this well before,” said Brock in amazement the next day.

“Yeah, I don't think you've fought even once today!” added Ash.

“Well,” replied May, in a mysterious tone of voice, “we had a sibling bonding experience. Isn't that right, Max?”

Max laughed and said, “Sure thing!” The two then giggled together at their own private knowledge, and Ash and Brock just watched them in confusion.

 


End file.
